Havana keeps saying that it's willing
to let this U.S. contractor go. But the White House and Congress keep rejecting
the offers.

Four years ago, Cuban security agents arrested an American subcontractor named Alan Gross, accused him of spying for the U.S., and sentenced him to 15 years in a Havana prison. Gross has been languishing there ever since, a victim of Obama administration inaction, Congressional meddling, and the difficulties of negotiating with a regime as mercurial and opaque as the government of Cuban strongman Raúl Castro.

The story of Gross’s continuing imprisonment — his sentence is set to run for 11 more years — offers a case study of Cuba’s potency as a political issue on Capitol Hill, where powerful lawmakers have helped block at least one deal that could have brought the contractor home. The White House, for its part, has shown little interest in substantive negotiations with the Cubans, in part because Havana’s demands have shifted considerably over the years. Gross, who traveled to Cuba to deliver satellite phones and other communications equipment to the island’s small Jewish community, has lost nearly 100 pounds and watched, from less than 100 miles away, as his daughter developed breast cancer and his 90-year-old mother’s health deteriorated sharply because of her own battle with lung cancer. Barring something unforeseen, he’ll never see her again.

The Gross case isn’t simply about the fate of a single American. U.S.-Cuban relations have been frozen for years, but President Obama took office in 2009 with what seemed like a clear political mandate to change that. He had won Florida after taking more of the Cuban-American vote than any Democrat in decades, and the White House quickly began exploring concrete ways of relaxing the sanctions, making it easier for Cuban-Americans to travel home, and improving diplomatic ties between the two countries. Those efforts were largely put on ice after Gross was arrested and sentenced, and it’s not clear when, or if, they’ll resume.

The latest twist in the saga is just spinning up now, with a loose-knit coalition of roughly 50 senators from both parties working to finalize a letter to the White House that uses some of the most forceful language to date to press President Obama to cut a deal with Havana. The letter, obtained by Foreign Policy, calls on Obama to "take whatever steps are in the national interest" to get Gross, 64, out of Cuba.

An earlier draft, portions of which were also obtained by FP, was far more explicit in calling for a negotiated settlement, with lawmakers pressing Obama to take "any measures necessary" to free Gross. People familiar with the matter say that the language was softened because of strong opposition from two of the most powerful and prominent members of the Senate, both of Cuban-American descent: Robert Menendez of New Jersey, the Democratic chairman of the Senate Foreign Relations Committee, and Republican Marco Rubio of Florida, who is widely seen as a likely contender for the GOP presidential nomination in 2016.

People involved in the Senate deliberations say that Menendez and Rubio have also been privately lobbying some of the 50 senators who have expressed a willingness to sign on to the letter to reconsider their support and remove their names. Legislative aides who have been working the issue expect at least a handful of the original signatories to drop off before the letter gets to the White House.

"Menendez and Rubio have been explaining to members that the original letter seemed innocuous, but it was really calling for the Obama administration to make more concessions to Castro," said Mauricio Claver-Carone, the director of the U.S.-Cuba Democracy PAC and a close ally of the two senators. "They’re making the case that we’ve been negotiating with the Cubans for four years, that it hasn’t worked, and that its time to impose consequential actions on Cuba until it frees Alan Gross."

The two lawmakers are pressing their case in a White House letter of their own. The letter, obtained by FP, calls for Obama to work towards Gross’s "immediate and unconditional release," as opposed to holding any negotiations — or making any concessions — to bring it about. The seven other signatories include New York Democrat Chuck Schumer and an array of Cuba hawks like Arizona Republican John McCain and South Carolina Republican Lindsey Graham. A Menendez aide said the letter will be delivered Friday.

The Gross case is so sensitive that none of the lawmakers and Capitol Hill staffers involved in the internal government deliberations over his release or the talks with the Cubans would speak for the record. The White House declined to comment and referred questions to the State Department, where a spokesperson said "securing Alan Gross’s immediate release is a top priority of the U.S."

"We use and will continue to use every appropriate diplomatic channel to press for Mr. Gross’s release, both publicly and privately," the spokesperson said.

Gross’s lawyer, Scott Gilbert, said the administration could be doing far more. Gilbert said the White House had erred by arguing that the Cuban government should release Gross unconditionally before Washington would address the broader U.S.-Cuba relationship while simultaneously calling for an improvement in U.S.-Cuban relations in order to then bring about his freedom.

"You have a self-created ‘Catch-22,’" he said.

The chain of events that would ultimately end with Gross’s arrest began fifteen years ago with the passage of the Helms-Burton Act, a hard-hitting bill that formalized the decades-old, and largely ineffective, U.S. embargo against Cuba. Congress approved the bill in March 1996, just weeks after Cuban MiG warplanes shot down a pair of small planes operated by a U.S.-based dissident group called Brothers to the Rescue, killing the four people aboard.

"In their memory, I will continue to do everything I can to help the tide of democracy that has swept our entire hemisphere finally, finally reach the shores of Cuba," President Clinton said at the time.

The legislation directed the U.S. Agency for International Development to devote more resources to democracy promotion work in Cuba, and the George W. Bush administration created a program designed to help ordinary Cubans evade the Castro regime’s strict controls on their phone and Internet usage. The money devoted to that initiative jumped from $3.5 million in 2000 to $20 million in 2009. A Bethesda-based firm called Development Alternatives, Inc., or DAI, received much of that funding. DAI, in turn, hired Gross to bring satellite phones and other communications equipment to Cuba. He began traveling to the island in early 2009.

Gross’s ordeal began on the night of December, 2009, just minutes after he finished a phone call with his wife Judy. He was slated to fly home the next day, but Gross never left Cuba. Instead, according to a detailed account in Foreign Affairs, four Cuban security agents knocked on the door of Gross’s room in Havana’s Hotel Presidente and arrested him as soon as he opened it up. They took him to a waiting car and drove him to a nearby military base. He has been in jail ever since.

Gross has acknowledged bringing satellite phones and other sensitive communications equipment into Cuba, but said he was simply trying to make it easier for the island’s small Jewish community to connect with the outside world over the Internet. In court testimony and media appearances, Gross said that he wasn’t aware that he was doing anything illegal.

The Cuban government, however, said that Gross was a sp
y who had been sent to Cuba to help ordinary citizens break the laws of their country. Cubans need formal permission from the government to use satellite phones or to connect to the Internet. The Cuban government moved Gross to a military prison and prepared to put him on trial.

Backchannel negotiations for Gross’s release had begun shortly after his arrest. People familiar with the matter say that the Cuban government initially indicated that it would consider releasing Gross if the American pro-democracy programs on the island were eliminated or sharply cut back. These people say that USAID quietly agreed to spend only $15 million of the $20 million that had been budgeted for the programming in 2010. The agency also said it would spend just $10 million of the money the following year, these sources said. Gross’s supporters would later point out that $10 million seemed like an astonishingly small amount of money to pay to get an American citizen out of a third-world jail.

A person with direct knowledge of the talks said that word of the changes leaked to Menendez and Republican Representative Ileana Ros-Lehtinen of Florida, a Cuban-American who was then the ranking member of the House Foreign Affairs Committee. Both lawmakers opposed making any concessions whatsoever to the Cuban government. "Menendez communicated to the White House, very bluntly, that there would be serious repercussions if the money wasn’t spent," this person said. USAID duly spent the full $20 million set aside for 2010. It would ultimately spend $20 million in 2011 as well.

Talks between the U.S. and Cuba continued, hampered by the levels of mistrust and hostility that had built up over the past few decades. In the fall of 2010, according to Foreign Affairs, then-Assistant Secretary of State Arturo Valenzuela met with Cuban Foreign Minister Bruno Rodriguez in New York to discuss the case. Valenzuela, according to Foreign Affairs, said Cuba had to release Gross before Washington would be willing to discuss other aspects of the U.S.-Cuba relationship. Rodriguez, the magazine reported, was angry that Valenzuela was laying down preconditions without making any promises of his own. The meeting ended without a deal. Valenzuela, now a professor at Georgetown, didn’t respond to repeated requests for comment.

Gross’s trial began in Havana in March 2011. He apologized to the Cuban government and insisted that he hadn’t been trying to subvert Cuban law or weaken the powers of the Castro government.

"I do deeply regret that my actions have been misinterpreted as harmful and a threat against the security and independence of Cuba," Gross said in a transcript of his hearing later released by one of his attorneys. "I am deeply sorry for being a trusting fool. I was duped. I was used. And my family and I have paid dearly for this."

The court decided Gross hadn’t paid enough and sentenced him to 15 years in a Cuban prison, a surprisingly harsh punishment for an American citizen then in his early 60s. In November 2012, Gross and his wife Judy filed a $60 million lawsuit against his former employer, DAI, accusing the firm of failing to adequately prepare him for the challenges and dangers of working in Cuba. The family settled the lawsuit this past May, without publicizing the terms and with neither party admitting fault.

"We have been clear from day one that Alan’s safe return to his family is our first priority," DAI President and Chief Executive Officer Jim Boomgard said in a statement at the time. "Settling this litigation allows us to work together on that overriding goal, which should be the focus for everyone involved in this case."

Judy Gross, in the same statement, said she was "pleased" the company had committed itself to doing everything in her power to win her husband’s release.

"We want Alan back home, safe and sound," she said.

There’s no sign that will happen anytime soon, however. The on-again, off-again talks have foundered over the future of the so-called "Cuban Five," a quintet of Cuban intelligence officers who were convicted of espionage and a variety of other crimes in 2001. One of them, Gerardo Hernández, was linked to the February 1996 downing of the two civilian planes operated by Brothers to the Rescue, the U.S.-based dissent group. He and three others remain in prison. The fifth, a U.S. citizen named René González, was paroled in 2011 and was allowed to return to Cuba in April 2013 for his father’s funeral. A federal judge ruled that González could stay in Cuba permanently if he gave up his American citizenship.

Several Americans who have worked on the Gross case for years said the Cubans have repeatedly offered to hold talks over his fate without preconditions, but didn’t get a response from the Obama administration. Other Cuban officials indicated to U.S. representatives that any resolution of the Gross case would have to involve the freeing of one or more of the four Cubans. An American who was involved in earlier phases of the talks said that he thinks the Cubans might also have been open to a deal if the U.S. had agreed to give the men new trials or improve their living conditions. "We’re talking conjugal visits, things like that," the person said.

There appears to be little chance of that sort of swap happening. Secretary of State John Kerry, who held a secret meeting with Rodriguez, the Cuban foreign minister, during his time in the Senate, bluntly told the House Foreign Affairs Committee in April that the Obama administration wouldn’t be willing to release the Cuban prisoners in exchange for Gross. The contractor, he said, should instead be released on "humanitarian" grounds.

"They were and have been attempting to trade Alan Gross for the five spies that are in prison here in the U.S., and we’ve refused to do that because there’s no equivalency," he said. "Alan Gross is wrongly imprisoned, and we’re not going to trade as if it’s spy for spy."

Raul Castro, Cuba watchers say, doesn’t appear willing to accept anything less than the freeing of some or all of the four Cuban spies.

"Raul raised the cost of letting Alan go," said a Hill staffer with knowledge of the case. "The ask is now the Cuban Four; if gets less than that, he loses face. He’s boxed himself in and needs to be able to show something he’s not likely to get."

Last spring, Rodriguez sat down with Gilbert and Judy Gross in Havana and floated the idea of sending Gross back to the U.S. for a two-week parole so the contractor could see his dying mother. Gilbert said the talks never matured because U.S. representatives "weren’t given clear directives" from senior Obama administration officials about whether to pursue a deal.

While the tussling continues, Gross is languishing in a Cuban jail, where he spends 23 hours per day in a small cell that he shares with two other prisoners. Prison appears to be taking an enormous physical and mental toll. A lump on Gross’s shoulder led to a temporary cancer scare. He missed one of his daughter’s weddings and wasn’t there for her when she was diagnosed with breast cancer. His mother, 90, appears to be in the final stages of herlung cancer battle. Gross isn’t slated to be freed until 2024, when he will be 75 years old. Gilb
ert, his lawyer, said hope of an early release is the only thing keeping Gross alive. If the U.S. government doesn’t figure out a way of bringing the contractor home, Gilbert said that he expects his client to die in prison. "Keeping him there for 11 years would be a death sentence," Gilbert said.